1. "Letting my credit card debt skyrocket. In my defense, I was out of work and almost homeless. I paid them off, then did it again (this time I was just stupid). 'It's only a hundred bucks; I'll pay it off quick.' Then 10 grand later, it's, 'Holy shit, how did that happen?'"
2. "Going into debt for my parents. I took out extra student loans and dropped out of school a few times because they kept asking for money. I needed to work two jobs to support us. I put a new car under my name that eventually got repossessed because they said they would pay it but didn’t and dumped it on me. Turns out, they have a gambling addiction. Getting myself together now; I was such a pushover back then."
3. "Buying a 'money pit' house. It was an architecturally significant 1920s building with all kinds of interesting features. But the house was perpetually in need of expensive repairs and replacements."
4. "I thought I was helping a boyfriend through a rough time with his business. In reality, I was giving him the down payment on a house for him and his wife and kids."
5. "Listening to my wealthy ex-father-in-law when he said I shouldn’t bother to save for retirement. I was crying the blues about being able to afford groceries that month and make my regular contribution to my IRA. He said, 'You shouldn’t worry about that. After I croak, you’ll be set for life.' Note he’s my EX-father-in-law."
6. "Putting my ex on my credit card. I wanted to help build his credit, like I had with my mom. The dumbass maxed the $11K limit, of course. My 780 credit score, perfect history, and a great card all down the drain. I'm paying $400 a month for the foreseeable future in order to knock the balance down. And he gets away with it scot-free."
7. "In late 2007, I'd had enough of my job. I had been there 10 years and was done. I quit, thinking I could immediately replace my job. Had no clue about the upcoming recession and couldn’t find a job anywhere. I lost my savings, my retirement, then my house to foreclosure. It destroyed my credit. Eventually got a good job again (it took two years) and rented for seven years. Lesson: Don’t quit your job until you have a replacement lined up."
9. "I went on a two-week-long road trip to 'find myself' one spring break. I was in a bad place mentally. I just spent whatever wherever because it made me feel happy. Ran up all my debit and credit cards straight to the limits. I'm lucky I was able to make it back home only having to call my dad once for gas money, or else I would have been stranded somewhere in the Northeast USA."
"It has taken me over five years to pay off most of that debt, and more than a little of it ended up in collections because I just didn't know that I had to care about such things. Foolishness of youth. I have one more debt in collections that I will be paying off for years to come, but then I'm done."
10. "Smoking for 20 years. So much money up in smoke. When I quit, I was up to two packs a day. And I must've smoked a pack a day for 10 years. Plus the additional costs of health problems later in life. Yeah, biggest mistake of my life."
11. "Going to an expensive private college and the debt that went along with it. Easily the worst mistake of my life."
12. "Not having good enough credit to buy a house six years ago. My neighbor died, and their family wanted to sell me the house for $75K, but never having credit cards before my score was about 600, and I couldn't find anyone to give me a loan. The house is now worth $270K. I missed out on something that would have helped me the rest of my life all because I didn't have credit."
13. "Buying a house in hopes it would fix my marriage."
14. "Renting an apartment with a three-year contract. I had to move after a year because of work. Had to pay rent for another six months until the landlord fortunately decided to sell the apartment and released me from the contact. Worst. Deal. Ever."
15. "I dropped out of nursing school in my final semester. I’m paying a lot of money for a degree I didn’t get that can’t be transferred anywhere. I want to be really clear the regret is the debt. It’s not not finishing nursing school. That was undoubtedly the correct decision for me."
16. "Signing up for a timeshare while on a weeklong bender and forgetting about it. $15K down the drain."
17. "Buying my house. It was 2018, and we got a steal on it. But I was informed on December 1 that the company I worked for was bought out and we’d all be fired in January. I decided to go ahead and close on December 7 because I believed I’d find another job soon. I also made a down payment of $35,000, my entire life savings, to get the payment affordable. I didn’t find a job for five months, and it paid $20K less a year."
19. "Constant takeout during COVID lockdowns. But then again, we couldn’t get groceries delivered, and I was high risk so we couldn’t go in person. But we continued it long after that because it was convenient and our local Indian place was AMAZING!"
20. "At my first job, I waited about five years to start my 401(k) because I thought it would give me more negotiating power with pay raises if they thought I wasn’t as tied down to the company. In fact, it never came up, and they ended up thinking the opposite because I was so dumb to not do it. Set me back five years."
21. "Not sticking up for myself when I told the car rep I only wanted to put a certain amount down for a car. I got pressured into putting in much more and eventually lost the car because I wasn’t financially stable after that. I was 18 with nobody to come in with me, an easy target looking back."
22. "Cashing in a $15,000 401(k) at the age of 27. I lost about 40% to tax off the top. Worse yet, that $15K would be worth nearly $500,000 at nominal return on investment today."
23. "I 'followed my dreams' after college and made an average of about $20K/year until I was like 28–29 years old. I'm still playing catch up, and I make 10 times that now."
24. "Buying clothes I don’t like to fit in with people 'cause I didn’t really have a distinct style. Now that I do, I don’t have the money for it."
25. "Signing up for online gambling once it was legal in my state. I developed a severe addiction and got into debt, my parenting was affected, and I was super depressed. I’m doing much better now, and I’ve banned myself via the department of gaming in my state. Slowly getting my finances back on track."
26. "Going to grad school out of fear rather than because I really knew what I wanted. I was young and now have a lot more debt for a degree I didn’t really need. And I constantly worry about my future and hate my career. So many bad effects."
27. And finally, "Investing in Beanie Babies."
Have you ever made a big financial mistake? Tell us about it in the comments.
Note: Responses have been edited for length and/or clarity.